toluene-4-sulfonic acid in toluene Heating;

1: TFA 2: 1) Mg, 1,2-dibromopropane, 2) CuBr*Me2S / 1) THF, 2 h, 2) THF, 0 deg C to r.t. 3: 69 percent / DMSO, (COCl)2 / CH2Cl2 / 0.33 h / -78 °C 4: p-TsOH / toluene / Heating 5: NaOH, Bu4NHSO4 / CH2Cl2; H2O / 3 h / Ambient temperature 6: 1.2 M nBuLi / cyclohexane; hexane; diethyl ether 7: AcCl / 0.5 h 8: 85 percent / p-TsOH / toluene / Heating View Scheme

1: NaOH 2: 2.) sodium ethoxide / 1.) benzene; 2.) benzene/ethanol, rt., 2 h 3: 9.5 g / aq. sodium hydroxide / 2 h / 55 - 60 °C 4: 14 g / Mg / diethyl ether / 1 h / Heating 5: 1.3 g / conc. and gaseous HCl / dioxane / 2 h / 55 - 65 °C 6: 0.45 g / selenium dioxide / xylene / 8 h / Heating 7: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 8: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: 9.5 g / aq. sodium hydroxide / 2 h / 55 - 60 °C 2: 14 g / Mg / diethyl ether / 1 h / Heating 3: 1.3 g / conc. and gaseous HCl / dioxane / 2 h / 55 - 65 °C 4: 0.45 g / selenium dioxide / xylene / 8 h / Heating 5: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 6: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: 14 g / Mg / diethyl ether / 1 h / Heating 2: 1.3 g / conc. and gaseous HCl / dioxane / 2 h / 55 - 65 °C 3: 0.45 g / selenium dioxide / xylene / 8 h / Heating 4: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 5: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: 1.3 g / conc. and gaseous HCl / dioxane / 2 h / 55 - 65 °C 2: 0.45 g / selenium dioxide / xylene / 8 h / Heating 3: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 4: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: 0.45 g / selenium dioxide / xylene / 8 h / Heating 2: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 3: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: 2.) sodium ethoxide / 1.) benzene; 2.) benzene/ethanol, rt., 2 h 2: 9.5 g / aq. sodium hydroxide / 2 h / 55 - 60 °C 3: 14 g / Mg / diethyl ether / 1 h / Heating 4: 1.3 g / conc. and gaseous HCl / dioxane / 2 h / 55 - 65 °C 5: 0.45 g / selenium dioxide / xylene / 8 h / Heating 6: 1.) N-bromosuccinimide; 2.) triethylamine / 1.) CCl4, reflux, 2.5 h, irradiation; 2.) reflux, 6 h 7: 0.09 g / 57percent hydriodic acid / 3 h / Heating View Scheme

1: pyridine / 2 h / Heating 2: AlCl3, subl. / diethyl ether / 1 h / Heating View Scheme